Yeah, this approach looks more clear. I understand your idea.
I don't know how does the community use your project. In my architecture (Controllers -> Services -> Repositories) I use it in the Controllers layer only. So if previously I could use HttpPostedFile now I have to use HttpContext.Current.Request.Files. Not a big problem of course but also not clear.
What do you think about adding an option to ReflectionConfigurator something like this
new ReflectionConfigurator().UseHttpPostedFile(true)
or maybe
new ReflectionConfigurator().RegisterType(concreteType).UseHttpPostedFile()